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Synthesis of dihydropyridine and piperidine derivatives via an unexpected reaction of pyridine with acetyl chloride

Mannu, Alberto and Spanu, Pietro and Ulgheri, Fausta (2013) Synthesis of dihydropyridine and piperidine derivatives via an unexpected reaction of pyridine with acetyl chloride. In: 35. Convegno della Divisione di chimica organica della Società Chimica Italiana, 9-13 settembre 2013, Sassari, Italia. [S.l.], Società Chimica Italiana, Divisione di chimica organica. O6. Conference or Workshop Item.

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Abstract

Acetyl chloride reacts with pyridine to give a mixture of N-acetyl-1,4- and 1,2-dihydropyridyl acetic acid (1a,b) after water quenching. The reactioninvolves the formation of a zwitterionic ketene enolate intermediate which results from deprotonation of the acetyl moiety of the in situ formed N-acetyl pyridinium ion.
The effect on the reaction outcome of different parameters as temperature, pyridine/acetyl chloride molar ratio, and as Lewis acids and triflate counterion presence has been studied in detail, and a reaction mechanism has been proposed.

Item Type:Conference or Workshop Item (Lecture)
ID Code:9282
Status:Published
Uncontrolled Keywords:Acetyl chloride, reaction mechanism, piperidine derivatives
Subjects:Area 03 - Scienze chimiche > CHIM/04 Chimica industriale
Divisions:002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:Società Chimica Italiana, Divisione di chimica organica
Publisher Policy:Depositato per gentile concessione dell'Editore
Deposited On:04 Nov 2013 14:09

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